WO1997019953A3 - Neue lh-rh-antagonisten mit verbesserter wirkung - Google Patents

Neue lh-rh-antagonisten mit verbesserter wirkung Download PDF

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Publication number
WO1997019953A3
WO1997019953A3 PCT/DE1996/002171 DE9602171W WO9719953A3 WO 1997019953 A3 WO1997019953 A3 WO 1997019953A3 DE 9602171 W DE9602171 W DE 9602171W WO 9719953 A3 WO9719953 A3 WO 9719953A3
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WO
WIPO (PCT)
Prior art keywords
antagonists
new
disclosed
salts
improved effectiveness
Prior art date
Application number
PCT/DE1996/002171
Other languages
English (en)
French (fr)
Other versions
WO1997019953A2 (de
WO1997019953A8 (de
Inventor
Bernhard Kutscher
Michael Bernd
Thomas Beckers
Thomas Klenner
Peter-Paul Emig
Patricia-Marie Charpentier
Original Assignee
Asta Medica Ag
Bernhard Kutscher
Michael Bernd
Thomas Beckers
Thomas Klenner
Emig Peter Paul
Charpentier Patricia Marie
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to DE59611201T priority Critical patent/DE59611201D1/de
Priority to EP96945986A priority patent/EP0876337B1/de
Application filed by Asta Medica Ag, Bernhard Kutscher, Michael Bernd, Thomas Beckers, Thomas Klenner, Emig Peter Paul, Charpentier Patricia Marie filed Critical Asta Medica Ag
Priority to EE9800165A priority patent/EE04318B1/xx
Priority to DK96945986T priority patent/DK0876337T3/da
Priority to UA98063319A priority patent/UA65531C2/uk
Priority to AU18670/97A priority patent/AU706546B2/en
Priority to SI9630705T priority patent/SI0876337T1/xx
Priority to BR9611760-5A priority patent/BR9611760A/pt
Priority to SK629-98A priority patent/SK282760B6/sk
Priority to PL96326977A priority patent/PL186872B1/pl
Priority to JP9520054A priority patent/JP2000501083A/ja
Priority to NZ330521A priority patent/NZ330521A/xx
Priority to AT96945986T priority patent/ATE289588T1/de
Publication of WO1997019953A2 publication Critical patent/WO1997019953A2/de
Publication of WO1997019953A3 publication Critical patent/WO1997019953A3/de
Priority to IS4733A priority patent/IS1914B/is
Priority to NO19982366A priority patent/NO311023B1/no
Priority to US09/087,274 priority patent/US5942493A/en
Priority to HK99102272A priority patent/HK1016999A1/xx
Publication of WO1997019953A8 publication Critical patent/WO1997019953A8/de

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/23—Luteinising hormone-releasing hormone [LHRH]; Related peptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • A61P5/04—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/80—Acids; Esters in position 3
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
    • C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract

Die Erfindung betrifft neue LH-RH-Antagonisten, insbesondere Peptidomimetika und in einer Seitenkette modifizierte Peptide, Salze derselben mit pharmazeutisch akzeptablen Säuren sowie Verfahren zur Herstellung der LH-RH-Antagonisten und ihrer Salze. Die erfindungsgemäßen Peptide stellen Analoge des das luteinisierende Hormon freisetzenden Hormons (LH-RH) dar. Die erfindungsgemäßen Verbindungen weisen eine hohe antagonistische Potenz auf und sind frei von unerwünschten Nebenwirkungen, insbesondere frei von oedematogenen Wirkungen.
PCT/DE1996/002171 1995-11-28 1996-11-14 Neue lh-rh-antagonisten mit verbesserter wirkung WO1997019953A2 (de)

Priority Applications (17)

Application Number Priority Date Filing Date Title
JP9520054A JP2000501083A (ja) 1995-11-28 1996-11-14 改善された作用効果を有する新規ｌｈ―ｒｈ―拮抗剤
PL96326977A PL186872B1 (pl) 1995-11-28 1996-11-14 Nowi antagoniści LH-RH, preparat farmaceutyczny zawierający nowego antagonistę LH-RH oraz sposób otrzymywania nowych antagonistów LH-RH
NZ330521A NZ330521A (en) 1995-11-28 1996-11-14 New lh-rh antagonists with improved effectiveness
EP96945986A EP0876337B1 (de) 1995-11-28 1996-11-14 Neue lh-rh-antagonisten mit verbesserter wirkung
UA98063319A UA65531C2 (en) 1995-11-28 1996-11-14 Luteinising hormone releasing hormone antagonists with an improved effiiciency and a method for the preparation thereof
AU18670/97A AU706546B2 (en) 1995-11-28 1996-11-14 Novel LH-RH antagonists having improved action
SI9630705T SI0876337T1 (en) 1995-11-28 1996-11-14 New lh-rh antagonists with improved effectiveness
BR9611760-5A BR9611760A (pt) 1995-11-28 1996-11-14 Novos antagonistas lh-rh com efeito aperfeiçoado
SK629-98A SK282760B6 (sk) 1995-11-28 1996-11-14 Antagonista LH-RH, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
DE59611201T DE59611201D1 (de) 1995-11-28 1996-11-14 Neue lh-rh-antagonisten mit verbesserter wirkung
DK96945986T DK0876337T3 (da) 1995-11-28 1996-11-14 Nye LH-RH-antagonister med forbedret virkning
EE9800165A EE04318B1 (et) 1995-11-28 1996-11-14 Parendatud toimega LHRH antagonistid
AT96945986T ATE289588T1 (de) 1995-11-28 1996-11-14 Neue lh-rh-antagonisten mit verbesserter wirkung
IS4733A IS1914B (is) 1995-11-28 1998-05-05 Ný LH-RH mótlyf, framleiðsla þeirra og notkun, ásamt læknislyfjum sem innihalda samsetningarnar og framleiðsla þeirra
NO19982366A NO311023B1 (no) 1995-11-28 1998-05-25 Nye LH-RH-antagonister, deres fremstilling og anvendelser samt legemidler inneholdende forbindelsene og deres fremstilling
US09/087,274 US5942493A (en) 1995-11-28 1998-05-28 LH-RH antagonists having improved action
HK99102272A HK1016999A1 (en) 1995-11-28 1999-05-24 Novel lh-rh antagonists having improved action

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19544212A DE19544212A1 (de) 1995-11-28 1995-11-28 Neue LH-RH-Antagonisten mit verbesserter Wirkung
DE19544212.1 1995-11-28

Related Child Applications (1)

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US09/087,274 Continuation-In-Part US5942493A (en) 1995-11-28 1998-05-28 LH-RH antagonists having improved action

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WO1997019953A2 WO1997019953A2 (de) 1997-06-05
WO1997019953A3 true WO1997019953A3 (de) 1997-08-28
WO1997019953A8 WO1997019953A8 (de) 2002-09-26

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AT (1) ATE289588T1 (de)
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BG (1) BG64386B1 (de)
BR (1) BR9611760A (de)
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DE (2) DE19544212A1 (de)
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HK (1) HK1016999A1 (de)
HU (1) HUP9901656A3 (de)
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EP1268522B1 (de) 2000-03-14 2008-09-17 AEterna Zentaris GmbH Lh-rh-antagonisten, deren herstellung und verwendung als arzneimittel
DE19911771B4 (de) 1999-03-17 2006-03-30 Zentaris Gmbh LHRH-Antagonist, Verfahren zu seiner Herstellung und seiner Verwendung
US7005418B1 (en) 1999-09-23 2006-02-28 Zentaris Gmbh Method for the therapeutic management of extrauterine proliferation of endometrial tissue, chronic pelvic pain and fallopian tube obstruction
SE0100567D0 (sv) * 2001-02-20 2001-02-20 Astrazeneca Ab Compounds
CN104086632A (zh) * 2014-08-05 2014-10-08 杭州诺泰制药技术有限公司 一种制备西曲瑞克的方法

Citations (2)

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US5300492A (en) * 1988-02-10 1994-04-05 Tap Pharmaceuticals LHRH analogs
WO1994013313A1 (en) * 1992-12-04 1994-06-23 Abbott Laboratories 6-position modified decapeptide lhrh antagonists

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US5140009A (en) * 1988-02-10 1992-08-18 Tap Pharmaceuticals, Inc. Octapeptide LHRH antagonists
US5110904A (en) * 1989-08-07 1992-05-05 Abbott Laboratories Lhrh analogs
IL101074A (en) * 1991-03-14 1997-09-30 Salk Inst For Biological Studi GnRH ANALOGS AND THEIR PREPARATION
ATE144538T1 (de) * 1991-04-25 1996-11-15 Romano Deghenghi Lhrh-antagonisten
JP3568952B2 (ja) * 1992-12-18 2004-09-22 アボット・ラボラトリーズ ５位及び６位に修飾アミノアシル残基を有するｌｈｒｈ拮抗薬
IL108509A0 (en) * 1993-02-22 1994-05-30 Salk Inst For Biological Studi GnRH antagonist peptides

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US5300492A (en) * 1988-02-10 1994-04-05 Tap Pharmaceuticals LHRH analogs
WO1994013313A1 (en) * 1992-12-04 1994-06-23 Abbott Laboratories 6-position modified decapeptide lhrh antagonists

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DK0876337T3 (da) 2005-05-09
JP2000501083A (ja) 2000-02-02
ZA969987B (en) 1997-06-17
EE04318B1 (et) 2004-06-15
HUP9901656A3 (en) 2001-10-29
AR004354A1 (es) 1998-11-04
MX9804120A (es) 1998-09-30
HK1016999A1 (en) 1999-11-22
NO311023B1 (no) 2001-10-01
SK62998A3 (en) 1999-07-12
CZ135898A3 (cs) 1998-09-16
PL186872B1 (pl) 2004-03-31
KR100460165B1 (ko) 2005-06-01
NO982366L (no) 1998-05-25
BR9611760A (pt) 1999-10-05
PT876337E (pt) 2005-06-30
ATE289588T1 (de) 2005-03-15
ES2238704T3 (es) 2005-09-01
HUP9901656A2 (hu) 1999-08-30
WO1997019953A2 (de) 1997-06-05
DE19544212A1 (de) 1997-06-05
NZ330521A (en) 1999-01-28
BG102514A (en) 1999-04-30
DE59611201D1 (de) 2005-03-31
IS1914B (is) 2004-02-03
EP0876337B1 (de) 2005-02-23
SI0876337T1 (en) 2005-06-30
CZ290098B6 (cs) 2002-05-15
KR19990071864A (ko) 1999-09-27
AU706546B2 (en) 1999-06-17
IS4733A (is) 1998-05-05
IL119703A0 (en) 1997-02-18
WO1997019953A8 (de) 2002-09-26
CN1087283C (zh) 2002-07-10
EE9800165A (et) 1998-12-15
PL326977A1 (en) 1998-11-09
SK282760B6 (sk) 2002-12-03
AU1867097A (en) 1997-06-19
NO982366D0 (no) 1998-05-25
EP0876337A2 (de) 1998-11-11
IL119703A (en) 2001-04-30
CA2238570A1 (en) 1997-06-05
BG64386B1 (bg) 2004-12-30
CN1202882A (zh) 1998-12-23
UA65531C2 (en) 2004-04-15
RU2163910C2 (ru) 2001-03-10

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